Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 7744029Publication DOI: 10.1111/j.1432-1033.1995.0194l.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: oholst
fz-borstel.de
Institutions: Division of Biochemical Microbiology, Forschungsinstitut Borstel, Germany, Division of Biochemical Microbiology, Institut fur Experimentelle Biologie und Medizin, Forschungsinstitut Borstel, Germany, Department of Chemistry, Carisberg Laboratory, Copenhagen, Denmark
The lipopolysaccharide from the recombinant strain Escherichia coli F515-140 containing the cloned gene gseA [3-deoxy-D-manno-octulopyranosonic acid (Kdo) transferase] from Chlamydia psittaci 6BC was isolated and sequentially de-O-acylated and de-N-acylated. The products were separated by high-performance anion-exchange chromatography into three fractions, two of which contained a single compound. Their structures were elucidated by high-field NMR spectroscopy as α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 1) (tetrasaccharide bisphosphate) [Holst, O., Broer, W., Thomas-Oates, J. E., Mamat, U. & Brade, H. (1993) Eur. J. Biochem. 214, 703-710] and α-Kdo-(2→4)-[α-Kdo-(2→8)-]-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 4) (hexasaccharide bisphosphate). The third fraction comprised two pentasaccharide bisphosphates, which could be separated by affinity chromatography using an immobilized monoclonal antibody specific for the trisaccharide α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo. The bound fraction was identified as α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 2) [Holst, O., Broer, W., Thomas-Oates, J. E., Mamat, U. & Brade, H. (1993) Eur. J. Biochem. 214, 703-710], whereas the unbound fraction was identified as α-Kdo-(2→4)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-D-GlcN-(1→6)-α-D-GlcN 1,4'-P2 (compound 3). This novel Kdo tetrasaccharide extends our knowledge on multifunctional Kdo transferases.
Lipopolysaccharide, LPS, oligosaccharide, structure, core, gene, strain, Escherichia, Escherichia coli, acid, Kdo, transferase, phosphate, Chlamydia, recombinant, bisphosphate, Chlamydia psittaci, gseA, HPLC
Structure type: oligomer
Location inside paper: Fig. 2, compound 3
Trivial name: core-lipid A carbohydrate backbone, epitope I
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_140092,IEDB_141807,IEDB_150901,IEDB_150908,IEDB_151531
Methods: 13C NMR, 1H NMR, GLC-MS, 31P NMR, HPAEC, affinity chromatography
Biosynthesis and genetic data: genetic data
Comments, role: Parent molecule: LPS, Chlamydia psittaci, recombinant;
Related record ID(s): 2426, 2501, 2503, 2559, 4476, 6417, 25550
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GlycomeDB:
8360, CCSD:
46735, CBank-STR:16076
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
0,6,6,4,4 aXKdop 176.9 101.5 35.2 67.0 67.2 73.2 70.6 63.9
0,6,6,4 aXKdop 176.7 100.7 34.4 69.3 64.9 73.4 70.8 64.1
0,6,6 aXKdop 176.7 100.5 34.2 69.3 65.4 72.1 70.7 64.2
0,6,4 P
0,6 bDGlcpN 102.1 56.8 75.0 74.0 75.3 63.4
0 aDGlcpN 92.8 55.9 72.2 70.9 73.2 70.5
P
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 0,6,6,4,4 | aXKdop | 176.9 | 101.5 | 35.2 | 67.0 | 67.2 | 73.2 | 70.6 | 63.9 |
| 0,6,6,4 | aXKdop | 176.7 | 100.7 | 34.4 | 69.3 | 64.9 | 73.4 | 70.8 | 64.1 |
| 0,6,6 | aXKdop | 176.7 | 100.5 | 34.2 | 69.3 | 65.4 | 72.1 | 70.7 | 64.2 |
| 0,6,4 | P | |
| 0,6 | bDGlcpN | 102.1 | 56.8 | 75.0 | 74.0 | 75.3 | 63.4 | |
| 0 | aDGlcpN | 92.8 | 55.9 | 72.2 | 70.9 | 73.2 | 70.5 | |
| | P | |
|
There is only one chemically distinct structure:
Found 
report error